Five Writing Lessons from Derek Sivers (From Circus Performer to Entrepreneur to Writer)

04 Apr 2026 #writing #bookwriting

A weekend on YouTube led me to a writing channel, and then to rediscover Derek Sivers.

If you haven’t heard of him, he’s the definition of someone who reinvented their life. He went from circus performer to running CD Baby, an online distribution platform. After selling it, he now writes books. How to Live, is his most recent and popular.

Here’s what I learned binge-watching his interviews and reading his blog:

#1. Be the entertainer. Your writing and stories aren’t about you. They’re about how to help your readers.

#2. Write succinct books. Call it a tiny book, a mini book, or simply a short book, it’s your best ideas distilled. A short book shows respect for your readers’ time.

#3. Write essays then turn them into books. A book could be a single idea or a collection of multiple ideas.

Start your book by writing essays. Then compile the best ones into a book. You’ll have proven and validated ideas.

#4. Write to scale yourself. When you want to stop talking about a subject, write a book. Next asked again, point to the book. That’s why Derek wrote Anything You Want.

Like Derek, before retiring from coding, my goal is to write a trilogy. Street-Smart Coding is the second installment.

#5. Focus on writing sentences. Write each sentence on a separate line. Then, write something shorter than you could.